Self Guided Walking Holidays & Cycling Holidays


Walking in Tuscany

Walking Holidays in Tuscany

Our walking holidays in Tuscany include some of the finest walking Italy has to offer. Days spent walking through the breathtaking Tuscan landscape between fascinating renaissance towns and monasteries are a magical experience.

Discover the tastes and textures of this famous region; our range of walking holidays in Tuscany have been put together to showcase the, almost geometric, landscape of hills, vineyards and olive trees. Whilst walking through Tuscany you will have the chance to sample the delicious the food and wine which Tuscany is renowned for.

Visit the famous Tuscan Hill Towns or trek between the unforgettable towns of Florence and Siena. You can experience an immersive Tour of Chianti or combine the wonders of Tuscany and Umbria. Our Italy specialists can help you arrange extensions to Florence, Rome, Pisa, Siena or perhaps another walking holiday in Italy so please don't hesitate to get in touch to start planning your dream trip to Italy.

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Classic Tuscany Short Break

Spend 4 nights exploring Tuscany on foot, walking between atmospheric ancient hilltop towns of Volterra, San Gimignano, Colle Val D’ Elsa and Siena.

Duration: 5 Days & 4 Nights
Available: May - October
From £515

Hill Towns of Tuscany Highlights

Hill Towns of Tuscany Highlights is a captivating short break, capturing the best of the southern Tuscan landscape while walking between fascinating medieval and Renaissance towns.

Duration: 6 Days & 5 Nights
Available: March - October
From £750

Hill Towns of Tuscany

Walk through romantic southern Tuscany between idyllic hill top towns, including Montepulciano, Pienza, Montalcino and finally Siena. Your journey winds through a unique linear, almost geometric landscape of hills, vineyards and olive trees between Renaissance towns and medieval monasteries.

Duration: 8 Days & 7 Nights
Available: March - October
From £975

Tuscany: From Florence to Siena

Discover the magic of Chianti; old farmhouses, medieval villages, rows of cypress trees, quiet forests of oak, beach and chestnut, the lively atmosphere of an outside table on the piazza and the cherry flavours of a glass of Chianti Classico. This is the definitive Tuscany.

Duration: 8 Days & 7 Nights
Available: April - October
From £775

Classic Tuscany

A week under the Tuscan sun; with 3 days of walking between hill-top towns, with time to relax and explore Volterra, San Gimignano, Colle Val D’Elsa Monteriggioni and Siena.

Duration: 8 Days & 7 Nights
Available: May - October
From £735

Tuscany: Classic Chianti

Follow Tuscan trails through the unforgettable wine region of Chianti to Siena, whose historic centre is a UNESCO World Heritage Site.

Duration: 8 Days & 7 Nights
Available: April - October
From £915

Treasures of Tuscany & Umbria

Walk from the medieval and Renaissance hill-top towns of Siena and Pienza in Tuscany, on to historic Perugia in Umbria, and ending in iconic Florence. Nestled in the green heart of Italy, you’ll walk through landscapes of rolling hills, past soldier-straight lines of cyprus trees, through vineyards and olives groves.

Duration: 10 days & 9 nights
Available: Mid April - late October
From £1,110

Tuscany: Chianti in Luxury

Walk Tuscan wine trails through the timeless landscapes of Chianti to Siena, staying in luxury accommodations.

Duration: 7 Days & 6 Nights
Available: April - October
From £1,860

Tuscany: Classic Chianti Short Break

On this short break walking adventure in Tuscany discover the unforgettable and classic landscapes of the Chianti wine region.

Duration: 5 Days & 4 Nights
Available: April - October
From £595
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